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Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

ABSTRACT: Progress toward the synthesis of the microtubule-stabilizing agent, (-)-zampanolide, is reported. Construction of the 2,6-cis-tetrahydropyran ring was accomplished utilizing ether transfer methodology in conjunction with an intramolecular radical cyclization reaction. Efficient installation of the C16-C20 side chain relied on a one-pot cross-metathesis/olefination sequence, Sharpless epoxidation, and selective reduction of a vinyl epoxide.

SUBMITTER: Wilson MR

PROVIDER: S-EPMC3391338 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Wilson Matthew R MR Taylor Richard E RE

Organic letters 20120621 13

Progress toward the synthesis of the microtubule-stabilizing agent, (-)-zampanolide, is reported. Construction of the 2,6-cis-tetrahydropyran ring was accomplished utilizing ether transfer methodology in conjunction with an intramolecular radical cyclization reaction. Efficient installation of the C16-C20 side chain relied on a one-pot cross-metathesis/olefination sequence, Sharpless epoxidation, and selective reduction of a vinyl epoxide. ...[more]

PMID: 22720980

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